- Synthesis of Highly Substituted 3-Pyrrolin-2-ones from N,N-Disubstituted α-Amino Acids
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Highly functionalized 5-membered N-heterocyclic compounds, 4-aryl-3-chloro-5-methoxy-1-methyl-3-pyrrolin-2-ones, have been synthesized in moderate to high yields by the reaction of N,N-dimethylated aromatic α-amino acids with oxalyl chloride, followed by solvolysis with MeOH. The products possess a number of functional groups such as an amide, a mixed amido/alkoxy acetal, a vinyl halide, and an alkene and thus are promising candidates to be used as starting materials for the synthesis of diverse five-membered N-heterocyclic compounds.
- Samper Barceló, Víctor,Bienz, Stefan
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- Synthesis and pharmacology of site-specific cocaine abuse treatment agents: 2-Substituted-6-amino-5-phenylbicyclo[2.2.2]octanes
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A series of 2-substituted-6-amino-5-phenylbicyclo[2.2.2]octanes was synthesized and tested for inhibitor potency in [3H]WIN 35,428 (WIN) binding at the dopamine (DA) transporter and [3H]DA uptake assays. To demonstrate transporter se
- Javanmard, Sahar,Deutsch, Howard M.,Collard, David M.,Kuhar, Michael J.,Schweri, Margaret M.
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- Iron-Catalyzed Synthesis of 2-Aminofurans from 2-Haloketones and Tertiary Amines or Enamines
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The selective synthesis of heterocycles from readily available substrates and catalyzed by an abundant and environmental benign catalyst continues to be an attractive topic. In this communication, we report an interesting protocol for the synthesis of 2-aminofurans. Starting from 2-haloketones and tertiary amines, with abundant iron salt as the catalyst, various 2-aminofurans were produced in good yields. Control experiments were performed to understand the reaction pathway. Based on the identified reaction pathway, the substrates for this transformation can be extended from tertiary amines to enamines and even with better final yields. Finally, a formal three-component reaction can also be realized by forming the enamines in-situ from aldehydes and amines.
- Wang, Le-Cheng,Geng, Hui-Qing,Peng, Jin-Bao,Wu, Xiao-Feng
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p. 2605 - 2616
(2020/04/24)
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- An Efficient One–pot Procedure for the Direct Preparation of 4,5-Dihydroisoxazoles from Amides
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A Mo(CO)6 (molybdenumhexacarbonyl) catalyzed reductive functionalization of amides to afford 5-amino substituted 4,5-dihydroisoxazoles is presented. The reduction of amides generates reactive enamines, which upon the addition of hydroximinoyl chlorides and base undergoes a 1,3-dipolar cycloaddition reaction that gives access to the desired heterocyclic compounds. The transformation of amides is highly chemoselective and tolerates functional groups such as nitro, nitriles, esters, and ketones. Furthermore, a versatile scope of 4,5-dihydroisoxazoles derived from a variety of hydroximinoyl chlorides and amides is demonstrated. (Figure presented.).
- Slagbrand, Tove,Kervefors, Gabriella,Tinnis, Fredrik,Adolfsson, Hans
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supporting information
p. 1990 - 1995
(2017/06/09)
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- Facile preparation of pyrimidinediones and thioacrylamides: Via reductive functionalization of amides
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The development of an efficient protocol for the reductive functionalization of amides into pyrimidinediones and amino-substituted thioacrylamides is presented. Enamines are generated in a highly chemoselective amide hydrosilylation reaction catalyzed by
- Trillo, Paz,Slagbrand, Tove,Tinnis, Fredrik,Adolfsson, Hans
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supporting information
p. 9159 - 9162
(2017/08/17)
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- Catalytic reductive dehydration of tertiary amides to enamines under hydrosilylation conditions
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Tertiary amides are efficiently reduced to their corresponding enamines under hydrosilylation conditions, using a transition-metal-free catalytic protocol based on t-BuOK (5 mol %) and (MeO)3SiH or (EtO) 3SiH as the reducing agent. The enamines were formed with high selectivity in good-to-excellent yields.
- Volkov, Alexey,Tinnis, Fredrik,Adolfsson, Hans
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supporting information
p. 680 - 683
(2014/03/21)
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- Synthesis, characterisation and reactivity of 2-functionalised vinylstannanes
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The functionalised vinylstannanes of the type (E)/(Z)-Ph3SnCR′=CHYRn and (E)/(Z)-Ph3SnC(YRn)=CHR′ (YRn=NMe2, OEt, SMe, SEt; R′=Ph, Bu (n-butyl), Pe (n-pentyl), H) were prepared by non-catal
- Lébl,Hole?ek,Dymák,Steinborn
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- Titanium-Mediated Carbonyl Olefinations. 2. Benzylidenations of Carbonyl Compounds with Dibenzyltitanocene
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Mild thermolysis of carbonyl compounds with dibenzyltitanocene affords phenyl-substituted olefins, enol ethers, and enamines.
- Petasis, Nicos A.,Bzowej, Eugene I.
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p. 1327 - 1330
(2007/10/02)
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- Reaction of Thioaldehydes with Amines
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The reaction of phosphonium ylides with elemental sulfur gave thioaldehydes, which changed to the corresponding thioamides in good yields when treated with amines.When thioaldehydes containing α-hydrogens were treated with secondary amines, the corresponding enamines or reduction products were obtained.
- Okuma, Kentaro,Komiya, Yasuo,Ohta, Hiroshi
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p. 2402 - 2406
(2007/10/02)
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